Remember the freedom that came with a pair of wellies as a kid? You weren't worried about a little rain back then. So why are so many of us grown men afraid of pulling on the rubbers when clouds open up now? Perhaps we think the rain boot is neither mature nor sophisticated—especially if it involves tucking in our pants. But let's get real: waterproof footwear is the most practical option for those dreaded dreary days. And fortunately dapper styles, from Ilse Jacobsen's rugged lace-ups to Swims' felt-lined slip ons, offer options that will keep you warm, dry and looking effortlessly cool while the other guys try tiptoeing around the puddles.

The Wellington boot, named after Arthur Wellesley, the first Duke of Wellington, was designed in order keep his feet dry on the battlefield.